


Devil's Tail

by keefling



Category: Critical Role (Web Series)
Genre: Established Relationship, M/M, Tail Sex, Tails, Trans Male Character
Language: English
Status: Completed
Published: 2018-07-22
Updated: 2018-07-22
Packaged: 2019-06-14 16:29:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,717
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15392802
Author URL: https://archiveofourown.org/users/keefling/pseuds/keefling
Summary: Tiefling tails are wonderful things.





	Devil's Tail

**Author's Note:**

> So there's a Tiefling feat in 3.5 called "Ride the Devil's Tail" and the rest is self-explanatory. 
> 
> Caleb is a trans man in this fic and I use feminine-coded words to describe his genitals.

Caleb’s eyes followed Molly’s tail as it swished back and forth against the sheets.  Molly was sitting on the edge of the bed in the process of unlacing his boots so he could strip off the rest of his clothing.  A wide grin spread across Molly’s face when he caught Caleb staring.

“Curious, Caleb?” Molly asked, curling the tip in a _come hither_ motion.

“What?” Caleb tore his eyes away from the hypnotizing sway of the purple appendage, blushing when his eyes met Molly’s.

“You can touch it, you know.”

Caleb’s cleared his throat.  He knew nothing about tiefling tails, how sensitive they were, or if there was an underlying meaning behind having them touched   It was a series of questions on his list of research topics that he had yet found answers to.  Of course, he had a willing subject to study up close, if only Caleb could get past his nerves and just ask Molly.

“Are you sure?” Caleb asked, approaching the bed.

“Caleb.  We’ve been fucking for a whole month, my dear,” Molly said, chuckling.  “Please, don’t be shy.”

Caleb laughed nervously and kneeled beside Molly.  He wore one of Molly’s loose-fitting tunics as a night shirt.  He liked to keep his chest covered but did not mind if he flashed Molly a bit of ass when he climbed into bed.

“Where can I, ah, start?”  Caleb reached out a hand and trailed off.  Molly curled his tail around Caleb’s wrist and rested the tip in Caleb’s palm.  Caleb smoothed his thumb over the spade and found that it was hard like cartilage and soft on the outside.

Caleb ran his fingers down the narrow length of the tail.  He noticed first that there were subtle ridges that jutted out from Molly’s extended spinal column.  Caleb let his fingers glide over them, smiling to himself as he enjoyed the feeling of little the bumps passing under his fingertips.

Molly smiled at him in quiet adoration as Caleb played with Molly’s tail like a child with a new toy.  Caleb laid Molly’s tail over his lap. He gave it a tentative squeeze near the middle and gasped when Molly flexed his muscles against Caleb’s palms.

Molly leaned back on his hands while Caleb explored.  Caleb worked his way up to where the tail thickened to the point where Caleb could only touch his thumb and middle finger together as he held it.  Caleb heard a soft gasp from Molly when he touched closer to the base.

“Is this alright?” Caleb asked.

“More than alright,” Molly said, his voice a little shaky.  “Please, continue.”

Molly reclined with his knees up and his feet planted on the mattress.  Caleb had a full view of Molly’s cock and balls if he cared to look, but he was much more interested in the breathy noises he could pull from Molly when he stroked the base of his tail.

“It is sensitive, _ja?_ ” Caleb asked.  

“Mmm, very,” Molly hummed, closing his eyes.

A erotic chill ran down Caleb’s spine.  He was delighted to find that a tiefling tail—well, at least this tiefling’s tail—was an erogenous zone.  Caleb lied down on his stomach and danced his fingers up the base until he reached Molly’s ass.  Molly shivered and his thighs trembled.  Most telling of all was the way Molly’s cock bobbed to life in front of Caleb’s face.

“Oh, you like that?” Caleb teased.

“Fuck, yes I do,” Molly groaned.  “Touching the base of my tail feels almost as good as when you touch my cock.”

“Oh,” Caleb gasped.  “Why did you not tell me this before?”

Molly shrugged.  “I thought it would be more fun if you figured it out yourself.”

“Is that so?”  Caleb sat up and straddled Molly’s tail.  Even with those pupil-less red eyes, Caleb could tell that Molly’s gaze was trained on him, anticipating his next move.

“Do you want to have fun tonight, Mollymauk?” Caleb asked, staring him dead in the eyes while he made a show of licking his own fingers and palms.  

“Yes,” Molly hissed.  Caleb took the first few inches of Molly’s tail into spit-slick hands and began to twist them around it like he would do with a dick.

Caleb began sliding his fist up and down, essentially jacking off Molly’s tail.  Molly whimpered and Caleb could feel the muscles flex and hear the tail-tip thumping excitedly against the mattress behind him.  Heat pooled in Caleb’s abdomen, growing hotter the more Molly squirmed.

Caleb bowed his head and kissed the base, his nose grazing Molly’s balls and making Molly clench reflexively.  Caleb chuckled to himself as he kissed his way up the crack of Molly’s ass.  He took one of Molly’s balls into his mouth and sucked gently before kissing back down to refocus his attention to the sensitive base of the tail.

“ _Caaaleb,_ ” Molly whined, gripping the sheets with pale-knuckled fists.

“Yes, Mollymauk?” Caleb lifted his head and smiled up at Molly from between his legs.

“Touch me, darling?  Please?”

“I am touching you,” Caleb said, giving Molly’s tail a squeeze.  “It seems to have the same effect as when I touch your cock.  Why should you get both, while I get nothing at all?”

Molly released a shuddering breath.  Caleb was having too much fun teasing to give in already.

Suddenly, Caleb felt something graze between his legs.  He gasped and squeezed his thighs together, catching Molly’s tail between them.

“You’re wet, darling,” Molly purred.  “You really love my tail, don’t you?”

When Molly’s tail rested against Caleb’s slit, wet with desire and aching to be touched, it was Caleb’s turn to whimper.

“It loves you, too,” Molly said.  Caleb rolled his hips and moaned when his hardened clit brushed against the surface of Molly’s tail.  Caleb continued rubbing himself on the length while returning his attention between Molly’s legs.  He flicked his tongue between the juncture of Molly’s ass and tailbone, stopping occasionally to lick stripes up the base with the flat of his tongue.

“Hold still,” Caleb murmured with a hint of annoyance, slapping a hand down on Molly’s abdomen to keep his hips from bucking, to keep his hard dick from smacking against Caleb’s forehead.

Caleb continued to rut against Molly’s tail, moaning when Molly flexed it.  It slid smoothly between Caleb’s slick pussy lips, igniting his nerves and bringing Caleb closer to orgasm.  He panted hotly against Molly’s thighs, growing lightheaded from the musky smell that filled his nose with every breath.

“Gonna cum,” Caleb slurred between sloppy kisses to flushed purple skin.  “Gonna cum on your tail, Molly.  Come on, fuck me.  Make me cum.”

Molly thrusted his tail up, lifting Caleb’s hips as Caleb ground his clit down on one of the prominent ridges.  Caleb squeezed his thighs together and pitched forward as he came, crying on Molly’s stomach.  When Caleb stopped shaking, Molly let his tail fall to the bed.  

“Good boy,” Molly purred, reaching down to stroke Caleb’s sweaty hair.  “You’re beautiful when you cum.”

“You always say that,” Caleb said, turning his head so that he could speak and flash Molly a goofy, blissed-out smile.

“Because it’s true,” Molly insisted.  “I love to watch you fall apart.”

Caleb blushed and propped himself up on his elbows.  “I would like to watch you do the same,” he said, sucking a bruise into Molly’s thigh.

It did not take long to get Molly back where he was panting and squirming and gripping the sheets.  Caleb continued pumping his fist up and down the length of the tail while assaulting the base with licks and kisses and grazing teeth over sensitive flesh.  Molly’s cock dribbled precum down its length and balls.  The way Molly shook warned Caleb that he was close.

“Touch my cock, Caleb, please,” Molly whimpered.  “Please, I’m begging you, I need to cum.”

Caleb smiled wickedly and licked his lips.  He roughly squeezed Molly’s tail, making the tiefling hiss. 

“You will cum like this or not at all,” Caleb growled.  He watched the way Molly's cock throbbed with every tug of Caleb’s fist.  Possession gripped his heart; Molly was gorgeous, laid out before Caleb, clenching his thighs and slamming his tail against the bed, all because of what Caleb was doing to him.  Caleb dragged the teasing out as long as possible before he heard Molly start to sob above him.

“You have been so good, Mollymauk,” Caleb cooed.  “It is time for your reward.”

Caleb wrapped his lips around Molly’s cock head and sucked, moaning as it throbbed inside his mouth.  Caleb steeled himself after a warning cry from Molly, securing his lips around the length while Molly filled his mouth with hot cum.  Caleb swallowed in quick succession, hollowing his cheeks and fluttering his eyelashes, putting on a show for Molly. 

Caleb felt Molly go limp and he let Molly’s cock fall from his lips.  He wiped his mouth with the back of his hand and collapsed on the bed, looping his arms around Molly’s thighs and resting his head on Molly’s stomach.

“Fuck, Caleb,” Molly panted, stroking Caleb’s cheek with his knuckles.  Caleb simply smiled against Molly’s sticky skin, still relaxed from his own orgasm and completely smitten with the man in his bed.

“Love you,” Caleb muttered.  “And your tail.” He used the last of his energy to crawl up the bed and lie next to Molly.  He folded his arms in and tucked his head under Molly’s chin, demanding to be held.  Molly snaked an arm around Caleb’s shoulders and rested the other on Caleb’s hip,

“Love you too,” Molly replied.  “And that gods-damn sinful mouth of yours.”

Caleb laughed and snuggled into Molly’s warm side.  He kissed Molly’s breast before closing his eyes and listening to his partner’s heartbeat. 

“We are going to do that again,” Caleb decided.  “I am going to make you cum just by touching your tail next time.  Do you think you can do that, Mollymauk?”

“I will do anything for you, my love,” Molly said, curling his tail securely around Caleb’s ankle, “But be careful, you wouldn’t want to make me cum in my pants every time you brushed against my tail in public.”

Caleb smirked against Molly’s chest.  “I would never,” Caleb lied through his teeth. 

**Author's Note:**

> Much thanks to Jas for proofreading!


End file.
